The present invention relates to a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide, which are utilized as an active ingredient of herbicidal compositions, a process for producing the derivative and a herbicidal composition containing the derivative as a active ingredient. More in detail, the present invention relates to the derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the following formula (I): ##STR2## wherein R represents an alkyl group of 2 to 10 carbon atoms, which is substituted by fluorine atom(s), and X represents a hydrogen atom or a fluorine atom, a process for producing the derivative and a herbicidal composition containing the derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide as an active ingredient.
Rice plant, wheat, corn, etc. are important crops and the use of herbicide is indispensable for contriving the increased yield of these crops by protecting the crops from the damage due to weed plants.
That the derivatives of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide have the herbicidal function has been hitherto described in Japanese Patent Applications Laid-Open (KOKAI) Nos. 57-193406(1982), 58-185572(1983) and 59-98004(1984).
For instance, Japanese Patent Application Laid-Open (KOKAI) No. 57-193406(1982)(corresponding to U.S. Pat. No. 4,492,597) discloses a herbicidal composition containing as an active ingredient a derivative of 1,2,4-triazole represented by the formula: ##STR3## wherein R.sub.1 is a hydrogen atom, a fluorine atom, a chlorine atom, an iodine atom, a lower alkyl group having 1 to 3 carbon atoms, an alkyl group substituted with a fluorine atom, a nitro group or a methoxy group; R.sub.2 is a hydrogen atom, a chlorine atom or a methyl group; and R.sub.3 is a hydrogen atom or a methyl group.
In Japanese Patent Application Laid-Open (KOKAI) No. 59-98004(1984), disclosed is a herbicidal composition containing a derivative of 1,2,4-triazole represented by the formula: ##STR4## wherein R.sub.1 and R.sub.2 represent independently a hydrogen atom, a halogen atom, an alkyl group or a halogenoalkyl group; R.sub.3 is a hydrogen atom, a halogen atom or an alkyl group; and R.sub.4 is a cyano group, carbamoyl group, thiocarbamoyl group, N-alkylcarbamoyl group, N-halogenoalkylcarbamoyl group, N-methoxyalkylcarbamoyl group, N-alkenylcarbamoyl group, N-halogenoalkenylcarbamoyl group, N-acylcarbamoyl group, N-halogenoacylcarbamoyl group or N-methylthiocarbamoylcarbamoyl group.
Also, Japanese Patent Application Laid-Open (KOKAI) No. 58-185572(1983) discloses a derivative of 1,2,4-triazole represented by the formula: ##STR5## wherein R.sup.1 represents a hydrogen atom or an alkyl group; m represents 0, 1 or 2; R.sup.2 represents an alkyl group, an alkoxyl group, a nitro group or a halogen atom; and n represents 1 or 2.
Further, the herbicide containing a derivative of 1,2,4-triazole has been proposed also in the following patents and patent applications.
U.K. Patent No. 2,120,665 discloses a herbicidal composition comprising a derivative of 1,2,4-triazole represented by the general formula: ##STR6## wherein R.sup.1 represents a hydrogen atom, a halogen atom or a (C.sub.1 -C.sub.2) alkyl group; R.sup.2 represents a hydrogen atom, a halogen atom, a (C.sub.1 -C.sub.2) alkyl group, a halogeno (C.sub.1 -C.sub.2) alkyl group, a methoxy group, a cyano group, a methoxymethyl group, a methylthio group, a methoxycarbonyl group or an isopropoxycarbonyl group; and R.sup.3 represents a thioamide group or a group represented by the general formula: ##STR7## wherein R.sup.4 represents a hydrogen atom, a (C.sub.1 -C.sub.2) alkyl group or a hydroxy (C.sub.1 -C.sub.2) alkyl group and R.sup.5 represents a hydrogen atom, a (C.sub.1 -C.sub.2) alkyl group, a halogeno (C.sub.1 -C.sub.2) alkyl group, a hydroxy (C.sub.1 -C.sub.2) alkyl group, a cyanomethyl group, an acetyl group, a halogenoacetyl group, a methoxyacetyl group, an amino group, a phenyl group, a methoxy group, a hydroxyl group, a (C.sub.2 -C.sub.3) alkenyl group, a halogeno (C.sub.2 -C.sub.3) alkenyl group, an isopropylcarbonyl group, a methylthiocarbonyl group or a 2-methoxyethyl group and a herbicidally acceptable carrier or diluent thereof.
European Patent No. 0,220,956 discloses a herbicidal composition comprising a 1,2,4-triazole-3-carboxamide compound represented by the formula: ##STR8## wherein R represents a straight-chain or branched-chain saturated (C.sub.2 -C.sub.10) alkyl group which is unsubstituted or substituted by fluorine atom(s); a cyclic saturated (C.sub.3 -C.sub.10) alkyl group which is unsubstituted or substituted by fluorine atom(s); a straight-chain, branched-chain or cyclic unsaturated (C.sub.3 -C.sub.10) alkyl group which is unsubstituted or substituted by fluorine atom(s); a group represented by the formula: ##STR9## where R.sup.1 represents a halogen atom, a (C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.3)alkoxy group or a fluorine-substituted (C.sub.1 -C.sub.3)alkyl group, m is 0 or an integer of from 1 to 5 and n is 0 or 1; a straight-chain or branched-chain saturated (C.sub.1 -C.sub.8)alkoxy(C.sub.2 -C.sub.10)alkyl group; a straight-chain or branched-chain unsaturated (C.sub.1 -C.sub.8)alkoxy(C.sub.2 -C.sub.10)alkyl group; a phenoxy(C.sub.2 -C.sub.6)alkyl group; an aralkoxy(C.sub.2 -C.sub.6)alkyl group; a phenoxy(C.sub.2 -C.sub.6)alkyl group having phenyl group(s) substituted by atom(s) or (C.sub.1 -C.sub.3)alkyl group(s); an aralkoxy halogen alkyl group having phenyl group(s) substituted by halogen atom(s) or (C.sub.1 -C.sub.3)alkyl group(s); a [(C.sub.1 -C.sub.8)alkoxy(C.sub.2 -C.sub.10)alkoxy](C.sub.2 -C.sub.10)alkyl group; or a group represented by the formula: ##STR10## wherein p is an integer of from 1 to 8, and a herbicidally acceptable carrier or adjuvant.
In U.S. patent application No. 07/042 321, proposed is a herbicidal composition comprising a herbicidally effective amount of a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the following formula as an active ingredient: ##STR11## wherein R.sup.1 represents a straight-chain alkyl group of 2 to 10 carbon atoms; a branched-chain alkyl group or cycloalkyl group of 3 to 10 carbon atoms; a (cycloalkyl)alkyl group of 4 to 10 carbon atoms; an unsubstituted or halogen-substituted phenyl group; an aralkyl group of 7 to 9 carbon atoms; an alkenyl group of 3 to 6 carbon atoms or an alkyl group of 2 to 10 carbon atoms, which has been substituted by 1 to 19 fluorine atoms, and R.sup.2 represents a fluorine atom, a chlorine atom, a methyl group or a methoxy group, and a herbicidally acceptable carrier or adjuvant.
In U.S. Pat. No. 4,973,353 filed Mar. 1, 1988 (corresponding to Japanese Patent Application No. 62-54579(1987) filed Mar. 10, 1987 and No. 62-153031(1987) filed Jun. 19, 1987), proposed is a herbicidal composition comprising as an active ingredient a herbicidally effective amount of a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the following formula: ##STR12## wherein R is a straight-chain alkyl group having 1 to 10 carbon atoms, which is an unsubstituted or substituted with 1 to 19 fluorine atoms; a branched alkyl group having 3 to 10 carbon atoms, which is an unsubstituted or substituted with 1 to 19 fluorine atoms; a cyclic alkyl group having 3 to 10 carbon atoms; an alkyl group having 1 to 3 carbon atoms which is substituted with an alicyclic structure having 3 to 7 carbon atoms; a phenyl group or an aralkyl group having 7 to 9 carbon atoms; X.sup.1 is a halogen atom or an alkyl group having 1 to 3 carbon atoms; X.sup.2 is a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Y.sup.1 is a hydrogen atom or a fluorine atom; and Y.sup.2 is a hydrogen atom or a fluorine atom, and herbicidally acceptable carrier or adjuvant.
The development of a compound excellent in selectivity in which the compound shows an excellent herbicidal activity only to the weeds without injuring the useful crops such as rice plant, wheat, corn, etc. is strongly demanded.
As a result of the present inventors' studies for offering a compound showing an excellent herbicidal effect and at the same time, does not injuring to the useful crops such as rice plant, wheat, corn, etc., it has been found out that a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the following formula (I) have the excellent herbicidal effect, and on the basis of this finding, the present invention has been attained. ##STR13## wherein R is an alkyl group of 2 to 10 carbon atoms, which is substituted by fluorine atom(s), and X represents a hydrogen atom or a fluorine atom.
The compound represented by the formula (I) is different from the compounds described in the aforementioned patents and patent applications in the point that the compound represented by the formula (I) has the group of --CH.sub.2 OR (wherein R represents the same meaning as above) at the 3-position of the phenyl group of the 5-position of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide, and the compounds represented by the formula (I) are the novel compounds.
Namely, the object of the present invention is provided with a derivative of 1,5-diphenyl1H-1,2,4-triazole-3-carboxamide which have the selectively herbicidal activity in which the derivative shows the excellent herbicidal function to the gramineous weeds and broad-leaved plants, particularly to the broad-leaved plants and on the other hand, does not shows any phytotoxicity to the crops such as rice plant, wheat, corn, etc. and the herbicidal composition containing the derivative thereof as an active ingredient.